Water → HCID 68288739, compound

HRID 541455Notes

Reaction equation

[CH:1]1([C:5]2[C:14]([C:15]#[CH:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:17])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.CCOC(C)=O.O.[Si]([N:29]=[N+:30]=[N-:31])(C)(C)C>>[CH:1]1([C:5]2[C:14]([C:15]3[CH:16]=[N:31][NH:30][N:29]=3)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:17])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Reactant 4

HCID 962Water

HCID 8857Ethyl Acetate

HCID 78378Azidotrimethylsilane

HCID 88923563HCID 88923563, compound2×

Product 1

HCID 68288739HCID 68288739, compoundYield 49%

Conditions

Temperature: 170 °C

Procedure

Methyl 4-cyclobutyl-5-ethynyl-2-methylbenzoate (compound 446.2, 180 mg, 0.69 mmol) was dissolved in TMSN3 (1 ml) in sealed tube. The reaction was heated to 170° C. for 24 hours behind a blast shield then cooled down to 0° C. EtOAc (10 ml) and water (20 ml) were added. The resulting mixture was stirred at RT for 1 hr. The organic phase was then washed with brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (SiO2; 0-30% EtOAc in Hexane) to give 92 mg (49%) of the title compound as a liquid. m/z (ES+) (272) (M+H)+. 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.83 (s, 1H), 7.35 (s, 1H), 3.90 (s, 4H), 2.69 (s, 3H), 2.27-2.15 (m, 2H), 2.13-2.03 (m, 2H), 1.99-1.90 (m, 1H), 1.86-1.76 (m, 1H).

Workup

temperaturethen cooled down to 0° C
washThe organic phase was then washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by flash chromatography (SiO2; 0-30% EtOAc in Hexane)

Sources & evidence

ORD record: ord-125997af83bf4dbf963bb0e2c2d83ea1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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